3-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-9-hydroxy-2-methylpyrido[1,2-a]pyrimidin-4-one → Paliperidone

HRID 448535Notes

Reaction equation

HRID 448535 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]4[C:22](=[O:23])[N:21]5[CH:24]=[CH:25][CH:26]=[C:27]([OH:28])[C:20]5=[N:19][C:18]=4[CH3:29])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1>[Pt].[Pd].C(O)(=O)C>[CH3:29][C:18]1[N:19]=[C:20]2[N:21]([CH2:24][CH2:25][CH2:26][CH:27]2[OH:28])[C:22](=[O:23])[C:17]=1[CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([C:6]2[C:5]3[CH:30]=[CH:31][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 1

HCID 446025173-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-9-hydroxy-2-methylpyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 115237Paliperidone

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

In the step-b, the pyridine ring of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl]ethyl]-9-hydroxy-2-methyl-4H-pyrido-[1,2-a]pyrimidin-4-one, compound of formula-11, is reduced by a suitable reducing agent as defined earlier. Good yields were obtained on hydrogenation using palladium or platinum catalyst in acidic conditions. In the preferred embodiment the reaction was performed by hydrogenation using palladium catalyst in presence of acetic acid to provide pure paliperidone.

Workup

  1. customGood yields
  2. customwere obtained on hydrogenation

Sources & evidence

ORD record
ord-d4b4278f66ed4b56859946c4f2d53a6d
Source dataset
uspto-grants-2013_07
Patent number
US08481729B2

Reaction notes

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